Daunorubicin HCl

DNA topoisomerase II inhibitor CAS# 23541-50-6

Daunorubicin HCl

Catalog No. BCC5083----Order now to get a substantial discount!

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Quality Control of Daunorubicin HCl

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Chemical structure

Daunorubicin HCl

3D structure

Chemical Properties of Daunorubicin HCl

Cas No. 23541-50-6 SDF Download SDF
PubChem ID 62770 Appearance Powder
Formula C27H30ClNO10 M.Wt 563.98
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Daunomycin
Solubility DMSO : 125 mg/mL (221.64 mM; Need ultrasonic)
H2O : ≥ 34 mg/mL (60.29 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
SMILES CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)C)O)N)O.Cl
Standard InChIKey GUGHGUXZJWAIAS-QQYBVWGSSA-N
Standard InChI InChI=1S/C27H29NO10.ClH/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33;/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3;1H/t10-,14-,16-,17-,22+,27-;/m0./s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Daunorubicin HCl

DescriptionAnticancer agent that is clinically used to treat nonlymphocytic leukemia. Inhibits RNA and DNA synthesis and causes DNA fragmentation in vivo. Reduces tau mRNA levels in vitro.

Daunorubicin HCl Dilution Calculator

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Daunorubicin HCl Molarity Calculator

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Preparing Stock Solutions of Daunorubicin HCl

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.7731 mL 8.8656 mL 17.7311 mL 35.4623 mL 44.3278 mL
5 mM 0.3546 mL 1.7731 mL 3.5462 mL 7.0925 mL 8.8656 mL
10 mM 0.1773 mL 0.8866 mL 1.7731 mL 3.5462 mL 4.4328 mL
50 mM 0.0355 mL 0.1773 mL 0.3546 mL 0.7092 mL 0.8866 mL
100 mM 0.0177 mL 0.0887 mL 0.1773 mL 0.3546 mL 0.4433 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Daunorubicin HCl

Daunorubicin HCl is an inhibitor of DNA topoisomerase II [1].

Daunorubicin is an anthracycline antibiotic. It is also used as an effective chemotherapeutic agent against tumors especially acute myeloid leukaemia and acute lymphocytic leukaemia. Daunorubicin can affect the metabolism and synthesis of DNA and RNA. In the in vitro assay, daunorubicin inhibits the incorporation of thymidine and uridine into L1210 cells. It also inhibits the incorporation of labeled precursors into the isolated DNA and RNA from incubated cells. When treated with leukemic cells isolated from acute lymphocytic leukemia patients, daunorubicin significantly inhibits the biosynthesis of the DNA and RNA macromolecules [2, 3].

References:
[1] Hande K R. Etoposide: four decades of development of a topoisomerase II inhibitor. European Journal of Cancer, 1998, 34(10): 1514-1521.
[2] Momparler R L, Karon M, Siegel S E, et al. Effect of adriamycin on DNA, RNA, and protein synthesis in cell-free systems and intact cells. Cancer Research, 1976, 36(8): 2891-2895.
[3] Meriwether W D, Bachur N R. Inhibition of DNA and RNA metabolism by daunorubicin and adriamycin in L1210 mouse leukemia. Cancer research, 1972, 32(6): 1137-1142.

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References on Daunorubicin HCl

Disposition and metabolism of [14-14C] 4-demethoxydaunorubicin HCl (idarubicin) and [14-14C]daunorubicin HCl in the rat. A comparative study.[Pubmed:3456281]

Cancer Chemother Pharmacol. 1986;16(2):107-15.

The disposition of [14-14C]4-demethoxyDaunorubicin HCl ([14-14C]idarubicin HCl, [14C]IDR) and of [14-14C]Daunorubicin HCl ([14C]DNR) was studied in male Sprague Dawley rats. [14C]IDR was administered either IV at 0.25 mg/kg body weight or PO at 1 mg/kg body weight, whereas [14C]DNR was dosed IV at 1 mg/kg body weight. The main elimination route for both compounds was the bile, fecal excretion representing 0.75-0.8 times the total dose at 72 h. Radioactivity due to [14C]IDR-derived species is released by the tissues at a slower rate than activity derived from [14C]DNR. After IV treatment comparable plasma levels are obtained, but tissue radioactivity is markedly lower with [14C]IDR, in keeping with the lower dosage. The ratio of plasma to tissue radioactivity is even higher in animals treated PO with [14C]IDR, because of the more extensive metabolism after this route of administration. The 13-dihydro derivatives of both [14C]IDR and [14C]DNR are the main metabolites in tissues, but in the case of the former, products of phase II reactions become more important at later times in liver and kidney and in excreta.

Pharmacokinetics of CPX-351 (cytarabine/daunorubicin HCl) liposome injection in the mouse.[Pubmed:19009594]

J Pharm Sci. 2009 Jul;98(7):2540-8.

CPX-351 (cytarabine/daunorubicin liposome injection) is a liposomal formulation of a synergistic, fixed combination of the antineoplastic drugs cytarabine and daunorubicin for intravenous infusion. The two drugs are contained within the liposome in a 5:1 molar ratio, shown to be synergistic in vitro and in murine models of hematological malignancies. Mice were given a single intravenous dose of CPX-351 or conventional cytarabine and daunorubicin in saline and plasma and bone marrow were assayed for drug and lipid concentrations. A pharmacokinetic model was developed to assess the disposition of the coencapsulated drugs in mice, including the free and encapsulated fractions after measurement of the total plasma concentrations. Through the measurement of the loss of both encapsulated drug and liposomal lipid from the plasma, the routes of elimination, extravasation (uptake of encapsulated drugs into the tissues) and leak (passage of the drugs across the liposome membrane into the plasma), could be discerned. Knowing the leak rates from the liposome into the plasma and the plasma pharmacokinetics of the conventional drugs, the free drug concentrations could be predicted. The free concentrations in the bone marrow from the liposome leak in plasma could also be predicted using the bone marrow responses to the conventional drugs.

Signaling pathways activated by daunorubicin.[Pubmed:11493433]

Blood. 2001 Aug 15;98(4):913-24.

The anthracycline daunorubicin is widely used in the treatment of acute nonlymphocytic leukemia. The drug has, of course, been the object of intense basic research, as well as preclinical and clinical study. As reviewed in this article, evidence stemming from this research clearly demonstrates that cell response to daunorubicin is highly regulated by multiple signaling events, including a sphingomyelinase-initiated sphingomyelin-ceramide pathway, mitogen-activated kinase and stress-activated protein/c-Jun N-terminal kinase activation, transcription factors such as nuclear factor kappa B, as well as the Fas/Fas-ligand system. These pathways are themselves influenced by a number of lipid products (diacylglycerol, sphingosine-1 phosphate, and glucosyl ceramide), reactive oxygen species, oncogenes (such as the tumor suppressor gene p53), protein kinases (protein kinase C and phosphoinositide-3 kinase), and external stimuli (hematopoietic growth factors and the extracellular matrix). In light of the complexity and diversity of these observations, a comprehensive review has been attempted toward the understanding of their individual implication (and regulation) in daunorubicin-induced signaling. (Blood. 2001;98:913-924)

A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin.[Pubmed:10075079]

Biochem Pharmacol. 1999 Apr 1;57(7):727-41.

The mechanisms responsible for the antiproliferative and cytotoxic effects of the anthracycline antibiotics doxorubicin (Adriamycin) and daunorubicin (daunomycin) have been the subject of considerable controversy. This commentary addresses the potential role of DNA synthesis inhibition, free radical formation and lipid peroxidation, DNA binding and alkylation, DNA cross-linking, interference with DNA strand separation and helicase activity, direct membrane effects, and the initiation of DNA damage via the inhibition of topoisomerase II in the interaction of these drugs with the tumor cell. One premise underlying this analysis is that only studies utilizing drug concentrations that reflect the plasma levels in the patient after either bolus administration or continuous infusion are considered to reflect the basis for drug action in the clinic. The role of free radicals in anthracycline cardiotoxicity is also discussed.

Daunorubicin and doxorubicin, anthracycline antibiotics, a physicochemical and biological review.[Pubmed:6380596]

Biochimie. 1984 May;66(5):333-52.

Daunorubicin and doxorubicin, two antibiotics belonging to the anthracycline group, are widely used in human cancer chemotherapy. Their activity has been attributed mainly to their intercalation between the base pairs of native DNA. Complex formation between daunorubicin or doxorubicin with polydeoxyribonucleotides and DNAs of various base composition or chromatins has been investigated by numerous techniques. Many authors have tried to correlate biological and therapeutic activities with the affinity of the drugs for DNA or some specific sequences of DNA. In vivo these anthracycline drugs cause DNA damage such as fragmentation and single-strand breaks. The mechanism of action of anthracyclines involves the inhibition of RNA and DNA syntheses. There exists two limiting factors in the use of anthracyclines as antitumoral agents: a chronic or acute cardiotoxicity and a spontaneous or acquired resistance. In both cases, there is probably an action at the membrane level. It has to be noted that daunorubicin and doxorubicin have a particular affinity for phospholipids and that the development of resistance is linked to some membrane alterations.

Description

Daunorubicin Hydrochloride (Daunomycin Hydrochloride; RP 13057 Hydrochloride; Rubidomycin Hydrochloride) is a topoisomerase II inhibitor with potent antineoplastic activities. Daunorubicin Hydrochloride (Daunomycin Hydrochloride; RP 13057 Hydrochloride; Rubidomycin Hydrochloride) inhibites DNA and RNA synthesis in sensitive and resistant Ehrlich ascites tumor cells.

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